Multi-step reaction with 9 steps
1.1: 2,6-dimethylpyridine / dichloromethane / 2 h / 25 °C / Inert atmosphere
2.1: 10-camphorsufonic acid / methanol / 3 h / 25 °C / Inert atmosphere
3.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0 - 25 °C / Inert atmosphere; Molecular sieve
4.1: sodium hexamethyldisilazane / tetrahydrofuran; toluene / 0.5 h / 0 °C / Inert atmosphere
4.2: -78 - 0 °C / Inert atmosphere
5.1: p-toluenesulfonic acid monohydrate / methanol; dichloromethane / 3 h / 25 °C / Inert atmosphere
6.1: 1H-imidazole / dichloromethane / 1 h / 25 °C / Inert atmosphere
7.1: bis(cyclohexanyl)borane / tetrahydrofuran / 0 - 25 °C / Inert atmosphere
7.2: 1 h / 0 °C / Inert atmosphere
8.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 3 h / 25 °C / Inert atmosphere
9.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / water; tert-butyl alcohol / 0.5 h / 25 °C / Inert atmosphere
With
1H-imidazole; 2,6-dimethylpyridine; sodium chlorite; sodium dihydrogenphosphate; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; bis(cyclohexanyl)borane; 10-camphorsufonic acid; p-toluenesulfonic acid monohydrate; sodium hexamethyldisilazane; sodium hydrogencarbonate; Dess-Martin periodane; 4-methylmorpholine N-oxide;
In
tetrahydrofuran; methanol; dichloromethane; water; toluene; tert-butyl alcohol;
4.1: Wittig reaction / 4.2: Wittig reaction / 7.1: Hydroboration reaction;
DOI:10.1021/ja109533y